Ion exchange resins used in high pressure chromatography columns are desired that can withstand the relatively high pressures and/or high temperatures typically encountered. Higher pressures can often impart greater separation power. Such ion exchange resins are usually crosslinked to provide resilience to deformation or fracture under high pressure and/or high temperature conditions. For example, many commercially available ion exchange resins for high pressure separations are based on divinylbenzene crosslinked polystyrene that are functionalized to provide ionic groups. Such materials are described, for example, in Pepper, J. Appl. Chem., 1951, 1, 124.
Polymeric materials have been prepared using spirobisindane-containing materials. For example, Reaction Scheme A shows the reaction of 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane with 2,3,5,6-tetrafluoroterephthalonitrile to form a polymeric material with fused dioxin rings as linking groups. These polymers and their synthesis methods are described more fully, for example, in Budd et al., Chem. Commun., 2004, 230 and in U.S. Pat. No. 7,690,514 (McKeown et al.).
The polymerization times tend to be lengthy (e.g., several days) and the monomers used to form the polymers are often quite expensive.